TW202219240A - Organic electroluminescence element - Google Patents

Abstract

The purpose of the present invention is to provide an organic EL element having high efficiency, low drive voltage, and a long lifespan by using a material for an organic EL element having excellent hole injection/transport performance, excellent electronic blocking ability, and excellent stability and durability in a thin film state and further by combining the material with various materials for the organic EL element having excellent hole and electron injection/transport performance, excellent electronic blocking ability, and excellent stability and durability in a thin film state so that characteristics of the materials can be effectively exhibited. The present invention is an organic electroluminescence device which has at least a hole transport layer, a light emitting layer, and an electron transport layer from a positive electrode side between the positive electrode and the negative electrode in this order and in which the hole transport layer contains a triarylamine compound having a specific structure.

Description

organic electroluminescent element

The present invention relates to organic electroluminescence elements that are self-luminous elements suitable for various display devices; more specifically, to organic electroluminescence elements using specific aromatic amine compounds (hereinafter simply referred to as "organic EL elements").

Since an organic EL element is a self-luminous element, compared with a liquid crystal element, since it is bright, it is superior in visibility, and it can display clearly, so it has been actively studied.

In 1987, CWTang et al. of Eastman Kodak Company put into practical use an organic EL device using an organic material by developing a multilayer structure element in which various roles are assigned to each material. CW Tang et al. layered a phosphor capable of transporting electrons and an organic matter capable of transporting holes, and injected the charges of the two into the phosphor layer to make it emit light, thereby obtaining 1000 cd/m at a voltage below 10V High luminance of ² or more (for example, refer to Patent Document 1 and Patent Document 2).

So far, many improvements have been made for the practical application of organic EL devices, and the role of each layer in the laminated structure has been further subdivided. The electroluminescence element of the layer, the electron transport layer, the electron injection layer, and the cathode can achieve high efficiency and durability (for example, see Non-Patent Document 1).

In addition, in order to further improve the luminous efficiency, attempts have been made to utilize triplet excitons to study the utilization of phosphorescent light-emitting compounds (for example, refer to Non-Patent Document 2). Furthermore, devices utilizing light emission by thermally activated delayed fluorescence (TADF) have also been developed. In 2011, Adachi of Kyushu University et al. achieved an external quantum efficiency of 5.3% by a device using a thermally activated delayed fluorescent material (for example, refer to Non-Patent Document 3).

The light-emitting layer can generally be produced by doping a charge-transporting compound called a host material with a fluorescent compound, a phosphorescent compound, or a material that emits delayed fluorescence. As described in the above-mentioned non-patent literature, the selection of the organic material in the organic EL element greatly affects various characteristics such as the efficiency and durability of the element (for example, see non-patent literature 2).

In the organic EL element, the charges injected by the two electrodes are recombined in the light-emitting layer to obtain light emission, but the important thing is how to efficiently transfer the two charges of holes and electrons to the light-emitting layer, and it is necessary to make a carrier with excellent balance. element. In addition, by improving the hole injection property and the electron blocking property of blocking electrons injected from the cathode, the probability of recombination of holes and electrons is increased, and by confinement of excitons generated in the light-emitting layer, High luminous efficiency can be obtained. Therefore, the role played by the hole transport material is important, and a hole transport material with high hole injection properties, high hole mobility, high electron blocking properties, and thus high durability to electrons is required.

In addition, regarding the life of the element, the heat resistance or amorphousness of the material is also important. Materials with low heat resistance are thermally decomposed even at low temperatures due to the heat generated when the element is driven, resulting in material deterioration. In a material with low amorphousness, the crystallization of the thin film occurs even in a short time, and the device deteriorates. Therefore, high heat resistance and good amorphous properties are required for the material to be used.

As hole transporting materials hitherto used for organic EL elements, N,N'-diphenyl-N,N'-bis(α-naphthyl)benzidine (NPD) or various aromatic amine derivatives ( For example, refer to Patent Document 1 and Patent Document 2). Although NPD has good hole transporting ability, its glass transition point (Tg), which is an index of heat resistance, is as low as 96°C, and device characteristics are degraded due to crystallization under high temperature conditions (for example, see Non-Patent Document 4). . In addition, among the aromatic amine derivatives described in the above-mentioned patent documents, there are known compounds having excellent mobility with a mobility of holes of 10 ^-3 cm ² /Vs or more (for example, refer to Patent Document 1 and Patent Document 2). However, due to insufficient electron blocking property, part of the electrons penetrates the light-emitting layer, and it is impossible to expect an improvement in luminous efficiency. Material. Further, aromatic amine derivatives with high durability have been reported (for example, see Patent Document 3), but they are used as charge transport materials used as electrophotographic photoreceptors, and there is no example of use as organic EL elements.

As compounds that improve properties such as heat resistance and hole injection properties, aromatic amine compounds having a substituted carbazole structure have been proposed (for example, see Patent Document 4 and Patent Document 5), but these compounds are used for hole injection layers Or the device of the hole transport layer has been improved in heat resistance and luminous efficiency, but it is still not sufficient, and further lower driving voltage or higher luminous efficiency is required.

In order to improve the device characteristics of organic EL devices or increase the yield of device fabrication, a combination of materials with excellent hole and electron injection and transport properties, film stability or durability is sought, and holes and electrons can be regenerated with high efficiency. Combination, high luminous efficiency, low driving voltage, long life components.

In addition, in order to improve the device characteristics of organic EL devices, a combination of materials with excellent hole and electron injection and transport properties, film stability or durability, high carrier balance efficiency, low driving voltage, and long life is required. [Prior Art Literature] [Patent Literature]

Patent Document 1: US Patent US5792557 Patent Document 2: US Patent US5639914 Patent Document 3: US Patent US7799492 Patent Document 4: US Patent US8021764 Patent Document 5: US Patent US8394510 Patent Document 6: Korean Laid-Open Patent Publication No. 10-2018-0051356 Patent Document 7: European Patent EP2684932 [Non-patent literature]

Non-Patent Document 1: Proceedings of the 9th Symposium of the Society of Applied Physics, pp. 55-61 (2001) Non-Patent Document 2: Proceedings of the 9th Symposium of the Society of Applied Physics, pp. 23-31 (2001) Non-Patent Document 3: Appl. Phys. Let., 98, 083302 (2011) Non-Patent Document 4: 13~14 pages of drafts for the third regular meeting of the Organic EL Symposium (2006)

The object of the present invention is to use a material for an organic EL device which is excellent in hole injection and transport performance, electron blocking ability, stability or durability in a thin film state, and furthermore, the material and hole and electron injection and transport performance , Various materials for organic EL elements with excellent electron blocking ability, stability in thin film state, and durability are combined in a way that can effectively exert the characteristics of each material, thereby providing high efficiency, low driving voltage, long Longevity of organic EL elements.

Examples of physical properties to be possessed by the organic compound used in the present invention include (1) good hole injection properties, (2) high hole mobility, (3) stable thin film state, and (4) excellent heat resistance. Moreover, as a physical property which the organic EL element provided by this invention should have, for example, (1) luminous efficiency and electric power efficiency are high, (2) practical driving voltage is low, and (3) long life is mentioned.

Therefore, in order to achieve the above-mentioned object, the inventors of the present application have conducted intensive research on various triaromatic amine compounds, focusing on the characteristics of excellent hole injection and transport performance, film stability and durability of triarylamine compounds. By using a triarylamine compound having a specific structure as the material of the hole transport layer, the holes injected from the anode side can be transported efficiently. As a result, the present invention has been completed.

That is, the present invention provides the following organic EL element. 1) An organic electroluminescence element, which is located between an anode and a cathode and has at least a hole transport layer, a light-emitting layer, and an electron transport layer in this order from the anode side, wherein the hole transport layer contains the following general triaromatic amine compound represented by formula (1);

(式中，A表示下述一般式(2-1)所示1價基； B表示取代或無取代之芳香族烴基、取代或無取代之芳香族雜環基、或者取代或無取代之縮合多環芳香族基； C表示下述一般式(2-1)所示1價基、取代或無取代之芳香族烴基、取代或無取代之芳香族雜環基、或者取代或無取代之縮合多環芳香族基；) [hua 1]

(In the formula, A represents a monovalent group represented by the following general formula (2-1); B represents a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group, or a substituted or unsubstituted condensation Polycyclic aromatic group; C represents a monovalent group represented by the following general formula (2-1), a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group, or a substituted or unsubstituted condensation polycyclic aromatic group ;)

(式中，虛線部表示鍵結部位； R ₁表示氘原子、氟原子、氯原子、氰基、硝基、可具有取代基之碳原子數1~6之直鏈狀或分枝狀之烷基、可具有取代基之碳原子數5~10之環烷基、可具有取代基之碳原子數2~6之直鏈狀或分枝狀之烯基、可具有取代基之碳原子數1~6之直鏈狀或分枝狀之烷氧基、可具有取代基之碳原子數5~10之環烷氧基、取代或無取代之芳香族烴基、取代或無取代之芳香族雜環基、取代或無取代之縮合多環芳香族基、或者取代或無取代之芳氧基； n為R ₁之個數，表示0~3之整數；又，n為2或3時，複數個鍵結於同一苯環的R ₁彼此可為相同或相異，亦可經由單鍵、取代或無取代之亞甲基、氧原子、或者硫原子相互鍵結形成環； L ₁表示取代或無取代之芳香族烴、取代或無取代之芳香族雜環、或者取代或無取代之縮合多環芳香族基的2價； m為L ₁之個數，表示1~3之整數；又，m為2或3時，L ₁彼此可為相同或相異； Ar ₁及Ar ₂彼此可為相同或相異，表示取代或無取代之芳香族烴基、取代或無取代之芳香族雜環基、或者取代或無取代之縮合多環芳香族基。) [hua 2]

(In the formula, the dotted line part represents the bonding site; R ₁ represents a deuterium atom, a fluorine atom, a chlorine atom, a cyano group, a nitro group, a straight-chain or branched alkane with 1 to 6 carbon atoms that may have substituents group, cycloalkyl group with 5 to 10 carbon atoms that may have substituents, straight-chain or branched alkenyl groups with 2 to 6 carbon atoms that may have substituents, and 1 carbon atoms that may have substituents Linear or branched alkoxy groups of ~6, cycloalkoxy groups of 5 to 10 carbon atoms that may have substituents, substituted or unsubstituted aromatic hydrocarbon groups, substituted or unsubstituted aromatic heterocycles group, substituted or unsubstituted condensed polycyclic aromatic group, or substituted or unsubstituted aryloxy group; n is the number of R ₁ , representing an integer of 0 to 3; and, when n is 2 or 3, a plurality of The R ₁ bonded to the same benzene ring can be the same or different from each other, and can also be bonded to each other through a single bond, a substituted or unsubstituted methylene group, an oxygen atom, or a sulfur atom to form a ring; L ₁ represents substituted or unsubstituted Divalent of substituted aromatic hydrocarbons, substituted or unsubstituted aromatic heterocycles, or substituted or unsubstituted condensed polycyclic aromatic groups; m is the number of L ₁ , representing an integer from 1 to 3; and, m When it is 2 or 3, L ₁ can be the same or different from each other; Ar ₁ and Ar ₂ can be the same or different from each other, representing a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group, Or substituted or unsubstituted condensed polycyclic aromatic groups.)

2) The organic electroluminescence element according to the above 1), wherein the monovalent group represented by the above general formula (2-1) is a monovalent group represented by the following general formula (2-2);

(式中，Ar ₁、Ar ₂、L ₁、m、n及R ₁係與上述一般式(2-1)同樣定義。) [hua 3]

(In the formula, Ar ₁ , Ar ₂ , L ₁ , m, n, and R ₁ are defined in the same manner as in the general formula (2-1) above.)

3) The organic electroluminescence element according to the above 1), wherein the monovalent group represented by the above general formula (2-1) is a monovalent group represented by the following general formula (2-3);

(式中，Ar ₁、Ar ₂、n及R ₁係與上述一般式(2-1)同樣定義；p表示0或1。) [hua 4]

(In the formula, Ar ₁ , Ar ₂ , n and R ₁ are defined in the same manner as in the above-mentioned general formula (2-1); p represents 0 or 1.)

4) The organic electroluminescence element according to the above 1), wherein the monovalent group represented by the above general formula (2-1) is a monovalent group represented by the following general formula (2-4);

(式中，Ar ₁、Ar ₂係與上述一般式(2-1)同樣定義；p表示0或1。) [hua 5]

(In the formula, Ar ₁ and Ar ₂ are defined in the same manner as in the general formula (2-1) above; p represents 0 or 1.)

5) The organic electroluminescence device according to any one of 1) to 4) above, wherein the hole transport layer is composed of two layers of a first hole transport layer and a second hole transport layer, and the first hole transport layer is composed of two layers. A hole transport layer contains a triarylamine compound represented by the general formula (1).

基、呋喃基、吡咯基、噻吩基、喹啉基、異喹啉基、苯并呋喃基、苯并噻吩基、吲哚基、咔唑基、苯并

唑基、苯并噻唑基、喹

啉基、苯并咪唑基、吡唑基、二苯并呋喃基、二苯并噻吩基、萘啶基、啡啉基、吖啶基、及咔啉基等。其他，可由碳數6~30之芳基、或碳數2~30之雜芳基選擇。 As "substituted or unsubstituted aromatic hydrocarbon group", "substituted or unsubstituted aromatic heterocyclic group" or "substituted or unsubstituted aromatic heterocyclic group" represented by R ₁ in the general formulae (2-1) to (2-3) The "aromatic hydrocarbon group", "aromatic heterocyclic group" or "condensed polycyclic aromatic group" in the "condensed polycyclic aromatic group", specifically, for example, phenyl, biphenyl, triphenyl terphenylyl, naphthyl, anthracenyl, phenanthryl, indenyl, spirobifluorenyl, indenyl, pyrenyl, perylene, allenyl, triphenylenyl, pyridyl, pyrimidine base, three

base, furyl, pyrrolyl, thienyl, quinolyl, isoquinolyl, benzofuranyl, benzothienyl, indolyl, carbazolyl, benzoyl

azolyl, benzothiazolyl, quinoline

olinyl, benzimidazolyl, pyrazolyl, dibenzofuranyl, dibenzothienyl, naphthyridinyl, phenanthroline, acridine, and carboline. Others can be selected from an aryl group having 6 to 30 carbon atoms or a heteroaryl group having 2 to 30 carbon atoms.

Specific examples of the "aryloxy group" in the "substituted or unsubstituted aryloxy group" represented by R ₁ in the general formulae (2-1) to (2-3) include phenoxy, Biphenyloxy, bis-triphenoxy, naphthyloxy, anthraceneoxy, phenanthrenyloxy, indenyloxy, indenyloxy, pyreneoxy, peryleneoxy and the like.

As "a straight-chain or branched alkyl group having 1 to 6 carbon atoms that may have a substituent" represented by R ₁ in the general formulae (2-1) to (2-3), "a possibly substituted alkyl group""Cycloalkyl group with 5 to 10 carbon atoms" or "linear or branched alkenyl group with 2 to 6 carbon atoms that may have substituents""straight chain with 1 to 6 carbon atoms""Cycloalkyl group having 5 to 10 carbon atoms", or "straight-chain or branched alkenyl group having 2 to 6 carbon atoms", specifically, for example Methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-pentyl, isopentyl, neopentyl, n-hexyl, cyclopentyl, cyclohexyl, 1 -Adamantyl, 2-adamantyl, vinyl, allyl, isopropenyl, and 2-butenyl, etc.

As "a straight-chain or branched alkoxy group having 1 to 6 carbon atoms which may have a substituent" or "which may have a substituent" represented by R ₁ in the general formulas (2-1) to (2-3) In the cycloalkoxy group having 5 to 10 carbon atoms in the substituent group, the "linear or branched alkoxy group having 1 to 6 carbon atoms" or the "cycloalkoxy group having 5 to 10 carbon atoms"", specifically, methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, tert-butoxy, n-pentoxy, n-hexyloxy, cyclopentyloxy group, cyclohexyloxy, cycloheptyloxy, cyclooctyloxy, 1-adamantyloxy, 2-adamantyloxy and the like.

唑基、苯并噻唑基、喹

啉基、苯并咪唑基、吡唑基、二苯并呋喃基、二苯并噻吩基、咔啉基等芳香族雜環基。此等取代基亦可進一步經上述例示之取代基所取代。又，此等取代基與經取代之苯環、或複數個取代於同一苯環之取代基彼此，亦可經由單鍵、取代或無取代之亞甲基、取代或無取代之胺基、氧原子或者硫原子相互鍵結形成環。 "Substituted aromatic hydrocarbon group", "Substituted aromatic heterocyclic group", "Substituted condensed polycyclic aromatic group", "Substituted aromatic group" represented by R ₁ in the general formulae (2-1) to (2-3) "oxy", "optionally substituted linear or branched alkyl with 1 to 6 carbon atoms", "optionally substituted with 5 to 10 carbon atoms cycloalkyl", "optionally substituted with 5 to 10 carbon atoms" A straight-chain or branched alkenyl group having 2 to 6 carbon atoms as a substituent", "a straight-chain or branched alkoxy group having 1 to 6 carbon atoms that may have a substituent" or "a possible substituent The "substituent" in the substituted cycloalkoxy group having 5 to 10 carbon atoms", specifically, a deuterium atom, a cyano group, a nitro group; a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom. and other halogen atoms; silyl groups such as trimethylsilyl, triphenylsilyl, etc.; straight-chain or branched alkyl groups with 1 to 6 carbon atoms such as methyl, ethyl, and propyl; methoxy Linear or branched alkoxy groups with 1 to 6 carbon atoms such as radicals, ethoxy groups, and propoxy groups; alkenyl groups such as vinyl groups and allyl groups; aryloxy groups such as phenoxy groups and tolyloxy groups ; Benzyloxy, phenethoxy and other arylalkoxy groups; phenyl, biphenyl, triphenyl, naphthyl, anthracenyl, phenanthryl, indenyl, spirobifluorenyl, indenyl, pyrenyl , perylene, allenyl, biphenylene and other aromatic hydrocarbon groups or condensed polycyclic aromatic groups; pyridyl, thienyl, furanyl, pyrrolyl, quinolinyl, isoquinolinyl, benzoyl furanyl, benzothienyl, indolyl, carbazolyl, benzoyl

azolyl, benzothiazolyl, quinoline

Aromatic heterocyclic groups such as olinyl, benzimidazolyl, pyrazolyl, dibenzofuranyl, dibenzothienyl, and carboline. These substituents may also be further substituted with the substituents exemplified above. In addition, these substituents and the substituted benzene ring, or a plurality of substituents substituted on the same benzene ring, can also pass through single bonds, substituted or unsubstituted methylene groups, substituted or unsubstituted amine groups, oxygen groups Atoms or sulfur atoms are bonded to each other to form a ring.

"Substituted or unsubstituted aromatic hydrocarbon group", "substituted or unsubstituted aromatic heterocyclic group" and "substituted or unsubstituted aromatic heterocyclic group" represented by Ar ₁ and Ar ₂ in the general formulae (2-1) to (2-4) "Unsubstituted condensed polycyclic aromatic group" is the same as "substituted or unsubstituted aromatic hydrocarbon group", "substituted or unsubstituted aromatic hydrocarbon group", "substituted or unsubstituted aromatic hydrocarbon group" represented by R ₁ in the above general formulas (2-1) to (2-3) "Aromatic heterocyclic group" and "substituted or unsubstituted condensed polycyclic aromatic group" are the same.

"Substituted or unsubstituted aromatic hydrocarbon group", "substituted or unsubstituted aromatic heterocyclic group" and "substituted or unsubstituted condensed polycyclic aromatic group" represented by B and C in the general formula (1) , is the same as the "substituted or unsubstituted aromatic hydrocarbon group", "substituted or unsubstituted aromatic heterocyclic group" and "substituted or unsubstituted aromatic heterocyclic group" represented by R ₁ in the above general formulas (2-1) to (2-3) or unsubstituted condensed polycyclic aromatic group" is the same.

、吡咯、呋喃、噻吩、喹啉、異喹啉、苯并呋喃、苯并噻吩、吲哚啉、咔唑、咔啉、苯并

唑、苯并噻唑、喹

啉、苯并咪唑、吡唑、二苯并呋喃、二苯并噻吩、萘啶、啡啉、吖啶等。 As "substituted or unsubstituted aromatic hydrocarbon, substituted or unsubstituted aromatic heterocyclic ring, or substituted or unsubstituted condensed polycyclic ring" represented by L ₁ in general formulas (2-1) and (2-2) "Aromatic hydrocarbons" of "substituted or unsubstituted aromatic hydrocarbons", "substituted or unsubstituted aromatic heterocycles" or "substituted or unsubstituted condensed polycyclic aromatic groups" in "aromatic divalent groups" , "aromatic heterocycle" or "condensed polycyclic aromatic", specifically, for example, benzene, biphenyl, bi-triphenyl, bi-tetraphenyl, styrene, naphthalene, anthracene, acenaphthene, perylene, phenanthrene, indene , pyrene, triphenyl, pyridine, pyrimidine, three

, pyrrole, furan, thiophene, quinoline, isoquinoline, benzofuran, benzothiophene, indoline, carbazole, carboline, benzo

azole, benzothiazole, quinoline

Linen, benzimidazole, pyrazole, dibenzofuran, dibenzothiophene, naphthyridine, phenanthroline, acridine, etc.

Furthermore, as "substituted or unsubstituted aromatic hydrocarbon, substituted or unsubstituted aromatic heterocyclic ring, or substituted or unsubstituted condensation" represented by L ₁ in general formulas (2-1) and (2-2) "Polycyclic aromatic divalent group" means a divalent group obtained by removing two hydrogen atoms from the above-mentioned "aromatic hydrocarbon", "aromatic heterocycle" or "condensed polycyclic aromatic group". Moreover, as a "substituent group" when such a divalent group has a substituent, for example, the "substituted aromatic hydrocarbon group" represented by R ₁ in the above-mentioned general formulae (2-1) to (2-3), The "substituents" of the "substituted aromatic heterocyclic group" and the "substituted condensed polycyclic aromatic group" are the same, and all aspects may be the same.

The monovalent group represented by the general formula (2-1) representing A in the general formula (1) is preferably a monovalent group represented by the general formula (2-2), more preferably the general formula (2-3) The monovalent group shown is particularly preferably a monovalent group represented by the general formula (2-4).

Ar ₁ and Ar ₂ in the general formulae (2-1) to (2-4) are preferably "substituted or unsubstituted aromatic hydrocarbon group" or "substituted or unsubstituted condensed polycyclic aromatic group", More preferably, it is a substituted or unsubstituted phenyl group, a naphthyl group or a biphenyl group, and particularly preferably an unsubstituted or unsubstituted phenyl group or an unsubstituted naphthyl group.

As B in the general formula (1), preferably "substituted or unsubstituted aromatic hydrocarbon group" or "substituted or unsubstituted condensed polycyclic aromatic group", more preferably substituted or unsubstituted phenyl, naphthalene group, biphenyl group, phenanthrenyl group or fentanyl group.

As C in the general formula (1), preferably "substituted or unsubstituted aromatic hydrocarbon group" or "substituted or unsubstituted condensed polycyclic aromatic group", more preferably substituted or unsubstituted phenyl, naphthalene group, biphenyl group, phenanthrenyl group or fentanyl group.

The triarylamine compound represented by the general formula (1) used in the present invention has (1) good hole injection properties, (2) high hole mobility, (3) stable film state, and (4) excellent heat resistance Because of these properties, it can be suitably used as a constituent material of the hole transport layer of the organic EL device of the present invention.

In the organic EL device of the present invention, in which the triarylamine compound represented by the general formula (1) used in the present invention is used as a constituent material of the hole transport layer, the holes possessed by the triarylamine compound can be utilized to the maximum extent. For mobility, high efficiency, low driving voltage, and long life can be achieved by using a triarylamine compound with excellent amorphous properties and stable thin film state.

Furthermore, in the organic EL device of the present invention, when the hole transport layer is composed of two layers of a first hole transport layer and a second hole transport layer, the first hole transport layer contains the above-mentioned general The triaromatic amine compound represented by the formula (1) can prevent electron movement in addition to excellent hole injection properties, so that an organic EL device with higher efficiency and longer life can be realized.

Among the triaromatic amine compounds represented by the above-mentioned general formula (1) suitable for use in the organic EL device of the present invention, specific examples of preferable compounds are illustrated in FIGS. 1 to 9 , but are not limited to these compounds.

The triarylamine compound represented by the general formula (1) can be purified by: purification by column chromatography; adsorption and purification by silica gel, activated carbon, activated clay, etc.; recrystallization or crystallization by solvent; sublimation Purification method, etc. Identification of compounds can be performed by NMR analysis. As physical property values, it is preferable to measure the melting point, glass transition point (Tg), and HOMO level (ionization potential). The melting point is an indicator of vapor deposition, the glass transition point (Tg) is an indicator of film state stability, and the HOMO level is an indicator of hole transport or hole blocking. The compound used in the organic EL device of the present invention is preferably purified by column chromatography; adsorption and purification by silica gel, activated carbon, activated clay, etc.; recrystallization or crystallization method by solvent; sublimation purification After refining by method, etc., it is finally refined by the sublimation refining method.

The melting point and the glass transition point (Tg) can be measured, for example, using a powder with a high-sensitivity differential scanning calorimeter (manufactured by Bruker AXS, DSC3100SA).

The HOMO level can be obtained, for example, by forming a thin film of 100 nm on an ITO substrate and using an ionization potential measuring device (manufactured by Sumitomo Heavy Industries, Ltd., PYS-202).

As the structure of the organic EL device of the present invention, for example, an anode, a hole transport layer, a light-emitting layer, an electron transport layer, and a cathode are sequentially included on the substrate, or there is a hole between the anode and the hole transport layer. An injection layer, a hole blocking layer between the light emitting layer and the electron transport layer, and an electron injection layer between the electron transport layer and the cathode. In these multilayer structures, for example, it is also possible to have a structure of both a hole injection layer and a hole transport layer, a structure of both an electron injection layer and an electron transport layer, and the like. In addition, a structure in which two or more organic layers having the same function are laminated may be used, a structure in which two or more hole transport layers are laminated, a structure in which two light-emitting layers are laminated, and a structure in which two electron transport layers are laminated may be used. The composition of layers, etc.

As the structure of the organic EL device of the present invention, it is preferable that the hole transport layer is constituted by two layers of a first hole transport layer and a second hole transport layer. Since the main function of the first hole transport layer is to efficiently transport the injected holes to the light-emitting layer, it is preferable to contain the three shown in the above-mentioned general formula (1) which shows an appropriate energy level and has a good hole transport ability. More preferably, the aromatic amine compound consists of a triaromatic amine compound represented by the above-mentioned general formula (1). In addition, since the function of the second hole transport layer is to prevent electrons from the light emitting layer from penetrating to the side of the hole transport layer, it is preferably adjacent to the light emitting layer and has a function as an electron blocking layer. Such electron blocking is also strongly correlated with component lifetime. That is, the structure of the organic EL device of the present invention can more efficiently inject holes into the light-emitting layer, and seal the electrons injected into the light-emitting layer from the electron transport layer in the light-emitting layer, so that the light-emitting efficiency of the device can be further improved. life.

As the anode of the organic EL element of the present invention, ITO or an electrode material having a large work function such as gold can be used. As the hole injection layer of the organic EL element of the present invention, triphenylamine-based materials such as starburst triphenylamine derivatives, various triphenylamine tetramers, etc.; porphyrin compounds represented by copper phthalocyanine can be used ; Acceptor heterocyclic compounds such as hexacyanoazatriphenylene; coating-type polymer materials, etc.

The hole transport layer of the organic EL device of the present invention uses the triaromatic amine compound represented by the general formula (1) as a hole transport material. When the hole transporting layer is composed of two layers of the first hole transporting layer and the second hole transporting layer, the triarylamine compound represented by the general formula (1) is preferably used only for the first hole transport layer. As other hole-transporting materials that can be mixed with the triaromatic amine compound represented by the general formula (1), or used simultaneously, except for N,N'-diphenyl-N,N'-bis(m-tolyl) Aniline (TPD), N,N'-diphenyl-N,N'-bis(α-naphthyl)benzidine (NPD), N,N,N',N'-tetraphenylbenzidine, etc. Aniline derivatives, 1,1-bis[4-(bis-4-tolylamino)phenyl]cyclohexane (TAPC), triarylamine compounds, various triphenylamine derivatives, etc. compound of.

Furthermore, in the hole injection layer and the first hole transport layer, the commonly used material P for these layers can be doped with sambromophenylamine hexachloroantimony, or an alkene derivative (for example, refer to patent documents). 7), etc., and a polymer compound having a structure of a benzidine derivative such as TPD in part of its structure, etc.

As a material used for the second hole transport layer of the organic EL element of the present invention, for example, 4,4',4"-tris(N-carbazolyl)triphenylamine (TCTA), 9,9- Bis[4-(carbazol-9-yl)phenyl]pyridine, 1,3-bis(carbazol-9-yl)benzene (mCP), 2,2-bis(4-carbazol-9-ylbenzene) carbazole derivatives such as adamantane (Ad-Cz), 9-[4-(carbazol-9-yl)phenyl]-9-[4-(triphenylsilyl)phenyl]-9H - Compounds having an electron blocking effect, such as compounds having a triphenylsilyl group and a triaromatic amine structure represented by fluoride.

唑衍生物、聚對伸苯基伸乙烯基衍生物等。又，發光層可由主體材料與摻雜劑材料構成，較佳係使用蒽衍生物作為主體材料；其他，除了上述發光材料之外，亦可使用具有吲哚環作為縮合環之部分構造之雜環化合物、具有咔唑環作為縮合環之部分構造之雜環化合物、咔唑衍生物、噻唑衍生物、苯并咪唑衍生物、聚二烷基茀衍生物等。又，作為摻雜劑材料，可使用芘衍生物、喹吖酮、香豆素、紅螢烯、苝及此等之衍生物、苯并吡喃衍生物、茚并菲衍生物、若丹明衍生物、胺基苯乙烯基衍生物等。 As the light-emitting layer of the organic EL device produced by this invention, in addition to metal complexes of quinolinol derivatives such as _Alq3 , various metal complexes, anthracene derivatives, and bis-styrylbenzene derivatives can be used. , pyrene derivatives,

azole derivatives, poly-p-phenylene vinylene derivatives, etc. In addition, the light-emitting layer can be composed of a host material and a dopant material, preferably an anthracene derivative is used as the host material; other than the above-mentioned light-emitting materials, a heterocyclic ring having an indole ring as a partial structure of a condensed ring can also be used Compounds, heterocyclic compounds having a carbazole ring as a partial structure of a condensed ring, carbazole derivatives, thiazole derivatives, benzimidazole derivatives, polydialkylene derivatives, and the like. Further, as dopant materials, pyrene derivatives, quinacridones, coumarin, rubrene, perylene and derivatives thereof, benzopyran derivatives, indenophenanthrene derivatives, rhodamine can be used derivatives, aminostyryl derivatives, etc.

Moreover, a phosphorescent light-emitting body can also be used as a light-emitting material. As the phosphorescent light-emitting body, a phosphorescent light-emitting body of a metal complex such as iridium or platinum can be used. Host materials when using green phosphorescent emitters such as Ir(ppy) ₃ , blue phosphorescent emitters such as FIrpic and FIr6, and red phosphorescent emitters such as Btp ₂ Ir(acac), etc. As the host material, carbazole derivatives such as 4,4'-bis(N-carbazolyl)biphenyl (CBP), TCTA, and mCP can be used. As an electron-transporting host material, p-bis(triphenylsilyl)benzene (UGH2) or 2,2',2"-(1,3,5-phenylene)-para(1-benzene) can be used base-1H-benzimidazole) (TPBI) and the like.

In order to avoid concentration quenching, the doping of the phosphorescent light-emitting material to the host material is preferably performed by co-evaporation in the range of 1-30 wt% relative to the entire light-emitting layer.

Furthermore, as the light-emitting material, materials that emit delayed fluorescence, such as CDCB derivatives of PIC-TRZ, CC2TA, PXZ-TRZ, and 4CzIPN, can be used (for example, see Non-Patent Document 3).

衍生物、

二唑衍生物等具有電洞阻止作用的化合物。此等材料亦可兼為電子輸送層之材料。As the hole blocking layer of the organic EL element of the present invention, in addition to phenanthroline derivatives such as bath copper (BCP), or bis(2-methyl-8-quinoline)-4-phenylphenolaluminum (III) ( In addition to the metal complexes of quinolinol derivatives such as BAlq), various rare earth complexes, triazole derivatives, triazole derivatives, etc. can be used.

derivative,

Compounds with hole blocking effect, such as oxadiazole derivatives. These materials may also serve as materials for the electron transport layer.

衍生物、

二唑衍生物、吡啶衍生物、嘧啶衍生物、苯并咪唑衍生物、噻二唑衍生物、蒽衍生物、碳二亞胺衍生物、喹

啉衍生物、吡啶并吲哚衍生物、啡啉衍生物、矽咯(silole)衍生物等。 As the electron transport layer of the organic EL device of the present invention, metal complexes of quinolinol derivatives such as Alq ₃ and BAlq, various metal complexes, triazole derivatives, triazole derivatives, etc. can be used.

derivative,

oxadiazole derivatives, pyridine derivatives, pyrimidine derivatives, benzimidazole derivatives, thiadiazole derivatives, anthracene derivatives, carbodiimide derivatives, quinoline derivatives

Line derivatives, pyridoindole derivatives, phenanthroline derivatives, silole derivatives, etc.

As the electron injection layer of the organic EL device of the present invention, metal complexes of alkali metal salts such as lithium fluoride and cesium fluoride, alkaline earth metal salts such as magnesium fluoride, and quinolinol derivatives such as lithium quinolinol can be used , metal oxides such as alumina, or metals such as ytterbium (Yb), samarium (Sm), calcium (Ca), strontium (Sr), and cesium (Cs). Also, the electron injection layer can be omitted due to the preferred selection of the electron transport layer and the cathode.

Furthermore, in the electron injection layer or the electron transport layer, a material generally used for the layer can be further N-doped with a metal such as cesium.

As the cathode of the organic EL element of the present invention, an electrode material with a low work function such as aluminum, or an alloy with a lower work function such as magnesium-silver alloy, magnesium-indium alloy, and aluminum-magnesium alloy can be used as the electrode material.

The materials used in the layers constituting the organic EL element of the present invention may be formed individually, or may be mixed with other materials to be used as a single layer, or may be used as a layered structure or mixture of layers formed individually. A laminated structure of layers to be formed into a film, or a laminated structure of a layer to be formed alone and a layer of mixed film formation. These materials can be formed into thin films by well-known methods such as spin coating and inkjet methods in addition to vapor deposition. [Example]

Hereinafter, embodiments of the present invention will be specifically described by way of examples, but the present invention is not limited to the following examples.

[Synthesis Example 1] <Synthesis of bis(4-naphthalen-2-yl-phenyl)-(2',5'-diphenyl-biphenyl-4-yl)-amine (1-4)> In a reaction vessel, filled with bis(4-naphthalen-2-yl-phenyl)-amine: 10.0 g, 4-bromo-2',5'-diphenyl-biphenyl: 11.0 g, palladium(II) acetate ): 0.1 g, tris(tert-butyl)phosphine: 0.2 g, sodium tert-butoxide: 2.7 g, and the mixture was stirred under reflux in a toluene solvent for 3 hours. After standing to cool, the filtrate obtained by filtration was concentrated to obtain a crude product. The obtained crude product was crystallized and purified with a toluene/acetone mixed solvent to obtain bis(4-naphthalen-2-yl-phenyl)-(2',5'-diphenyl-biphenyl-4-yl )-amine (1-4) white powder: 9.0 g (yield: 52.3%).

[hua 6]

About the obtained white powder, the following 39 hydrogen signals were detected by ¹ H-NMR (CDCl ₃ ), and the structure was identified. δ(ppm)=8.06(2H), 7.92(6H), 7.78(4H), 7.73(1H), 7.68(5H), 7.53(7H), 7.42(1H), 7.39-7.23(9H), 7.14(4H) ).

[Synthesis Example 2] <Synthesis of (2',5'-diphenyl-biphenyl-4-yl)-(4-naphthalen-1-yl-phenyl)-phenanthren-9-yl-amine (1-58)> In a reaction vessel, charge (2',5'-diphenyl-biphenyl-4-yl)-(4-naphthalen-1-yl-phenyl)-amine: 8.5 g, 9-bromo-phenanthrene: 4.8 g, palladium (II) acetate: 0.1 g, tris(tert-butyl) phosphine: 0.3 g, sodium tert-butoxide: 2.3 g, and the mixture was stirred under reflux in a toluene solvent for 3 hours. After standing to cool, the filtrate obtained by filtration was concentrated to obtain a crude product. The obtained crude product was crystallized and purified with a toluene/acetone mixed solvent to obtain (2',5'-diphenyl-biphenyl-4-yl)-(4-naphthalen-1-yl-phenyl) -White powder of phenanthrene-9-yl-amine (1-58): 8.3 g (yield: 73.1%).

[hua 7]

About the obtained white powder, the following 37 hydrogen signals were detected by ¹ H-NMR (CDCl ₃ ), and the structure was identified. δ(ppm)=8.79(1H), 8.75(1H), 8.14(1H), 8.03(1H), 7.92(1H), 7.85(2H), 7.72(6H), 7.65(2H), 7.60(1H), 7.50(7H), 7.42(1H), 7.36(3H), 7.27-7.18(6H), 7.09(4H).

[Synthesis Example 3] <Synthesis of (2',5'-diphenyl-biphenyl-4-yl)-(4-naphthalen-2-yl-phenyl)-phenanthren-9-yl-amine (1-59)> In a reaction vessel, charge (2',5'-diphenyl-biphenyl-4-yl)-(4-naphthalen-2-yl-phenyl)-amine: 8.0 g, 9-bromo-phenanthrene: 4.5 g, palladium (II) acetate: 0.1 g, tris(tert-butyl) phosphine: 0.2 g, tert-butoxide sodium: 2.2 g, and the mixture was stirred under reflux in a toluene solvent for 3 hours. After standing to cool, the filtrate obtained by filtration was concentrated to obtain a crude product. The obtained crude product was crystallized and purified with a toluene/acetone mixed solvent to obtain (2',5'-diphenyl-biphenyl-4-yl)-(4-naphthalen-2-yl-phenyl) - Pale yellow powder of phenanthrene-9-yl-amine (1-59): 6.6 g (yield: 61.7%).

[hua 8]

About the obtained pale yellow powder, the following 37 hydrogen signals were detected by ¹ H-NMR (CDCl ₃ ), and the structure was identified. δ(ppm)=8.79(1H), 8.74(1H), 8.09(1H), 8.01(1H), 7.86(4H), 7.75(1H), 7.71(5H), 7.66(2H), 7.60(3H), 7.50(5H), 7.39(1H), 7.34-7.23(6H), 7.20(2H), 7.07(4H).

[Synthesis Example 4] <(2",5"-diphenyl-[1,1';4',1"]triphenyl-4-yl)-(4-naphthalen-2-yl-phenyl)-phenyl-amine Synthesis of (1-69)＞ In a reaction vessel, charged with (4-naphthalen-2-yl-phenyl)-phenyl-amine: 6.0 g, 4-bromo-2",5"-diphenyl-[1,1';4' ,1"] Bitriphenyl: 10.3g, Palladium(II) acetate: 0.1g, Tris(tert-butyl)phosphine: 0.2g, Sodium tert-butoxide: 2.3g, refluxed and stirred under toluene solvent for one night After cooling, the filtrate obtained by filtration was concentrated to obtain a crude product. The obtained crude product was purified by column chromatography (carrier: silica gel, eluent: dichloromethane/n-heptane) to obtain (2 ",5"-diphenyl-[1,1';4',1"]triphenyl-4-yl)-(4-naphthalen-2-yl-phenyl)-phenyl-amine (1- 69) white powder: 7.1 g (yield: 51.7%).

[Chemical 9]

About the obtained white powder, the following 37 hydrogen signals were detected by ¹ H-NMR (CDCl ₃ ), and the structure was identified. δ(ppm)=8.04(1H), 7.91(3H), 7.73(5H), 7.66(2H), 7.56(2H), 7.51(7H), 7.42(1H), 7.39-7.18(15H), 7.10(1H) ).

[Synthesis Example 5] <(2",5"-diphenyl-[1,1';4',1"]triphenyl-4-yl)-(4-phenanthren-9-yl-phenyl)-phenyl-amine Synthesis of (1-83)＞ In a reaction vessel, charged with (4-phenanthren-9-yl-phenyl)-phenyl-amine: 11.0 g, 4-bromo-2",5"-[1,1';4',1"] Bitriphenyl: 16.2 g, palladium (II) acetate: 0.1 g, tris(tertiary butyl) phosphine: 0.3 g, sodium tertiary butoxide: 3.7 g, refluxed and stirred under toluene solvent for one night. , the filtrate obtained by filtration was concentrated to obtain a crude product. The obtained crude product was purified by column chromatography (carrier: silica gel, eluent: dichloromethane/n-heptane) to obtain (2", 5" -Diphenyl-[1,1';4',1"]triphenyl-4-yl)-(4-phenanthren-9-yl-phenyl)-phenyl-amine (1-83) on white Powder: 11.2 g (yield: 48.5%).

[Chemical 10]

About the obtained white powder, the following 39 hydrogen signals were detected by ¹ H-NMR (CDCl ₃ ), and the structure was identified. δ(ppm)=8.81(1H), 8.75(1H), 8.09(1H), 7.93(1H), 7.71(7H), 7.65-7.44(10H), 7.44-7.22(17H), 7.11(1H).

硼烷：113.9g、甲苯：350mL、乙醇：88mL、碳酸鉀：80.4g、水：290mL，加入肆(三苯基膦)鈀：6.7g，回流攪拌14小時。放冷後分液，對有機層以水、飽和食鹽水依序洗淨，藉由無水硫酸鎂乾燥。藉由過濾去除乾燥劑，將濾液濃縮。對殘渣加入庚烷：450mL，於室溫攪拌一晚，藉由過濾採集固體，獲得[1,1’:2’,1”:4”,1”’-聯四苯基]-4-胺的黃白色粉體：77.8g(產率：83.3%)。 [Synthesis Example 6] <N-(3'-(naphthalene-2-yl)-[1,1'-biphenyl]-4-yl)-N-(4-(naphthalene)-2-yl)phenyl )-5'-phenyl-[1,1';2',1"-triphenyl]-4-amine (1-96) synthesis> In the reaction vessel, filled with 4-bromoaniline: 50.0g , 4,4,5,5-tetramethyl-2-[1,1';4',1"-triphenyl]-2'-yl-1,3,2-di

Borane: 113.9 g, toluene: 350 mL, ethanol: 88 mL, potassium carbonate: 80.4 g, water: 290 mL, tetra(triphenylphosphine)palladium: 6.7 g was added, and the mixture was stirred under reflux for 14 hours. After cooling, the layers were separated, and the organic layer was washed with water and saturated brine in this order, and dried over anhydrous magnesium sulfate. The drying agent was removed by filtration and the filtrate was concentrated. Heptane: 450 mL was added to the residue, stirred overnight at room temperature, and the solid was collected by filtration to obtain [1,1':2',1":4",1"'-bitetraphenyl]-4-amine The yellow-white powder: 77.8 g (yield: 83.3%).

[Chemical 11]

In the reaction vessel, fill [1,1':2',1":4",1"'-ditetraphenyl]-4-amine: 55.0 g, 2-(4-bromophenyl)naphthalene: 74.9 g, tert-butoxide sodium: 28.0 g, toluene: 420 mL, ginseng (dibenzylideneacetone) dipalladium: 0.9 g, 2,2'-bis(diphenylphosphino)-1,1'- Binaphthyl: 2.4g, reflux stirring for 15 hours. Cool to 80°C, use a funnel laid with diatomaceous earth to remove solids by hot filtration. The filtrate is heated and stirred, and silica gel: 50g is added at 80°C, stirred for 1 hour, and the The solid was removed by hot filtration. The filtrate was concentrated, and the residue was recrystallized from a toluene/acetone mixed solvent to obtain N-(4-(2-naphthyl)phenyl)-[1,1':2',1" : Yellow-white powder of 4",1"'-bitetraphenyl]-4-amine: 69.5 g (yield: 68.3%).

[Chemical 12]

In a reaction vessel, charge N-(4-(2-naphthyl)phenyl)-[1,1':2',1":4",1"'-bitetraphenyl]-4-amine: 69.5g, 1-bromo-4-iodobenzene: 45.1g, sodium tert-butoxide: 25.7g, toluene: 700mL, copper iodide: 2.5g, N,N'-dimethylethylenediamine: 2.3g , stirred at reflux for 16 hours. Cooled to 80° C., and the solid was removed by hot filtration using a funnel laid with diatomaceous earth. The filtrate was concentrated, and the residue was subjected to column chromatography (carrier: silica gel, eluent: dichloromethane). /n-heptane) was purified to obtain N-(4-bromophenyl)-N-(4-(2-naphthyl)phenyl)-[1,1':2',1":4",1 "'-bitetraphenyl]-4-amine yellow-white powder: 59.4 g (yield: 65.5%).

[Chemical 13]

In the reaction vessel, fill N-(4-bromophenyl)-N-(4-(2-naphthyl)phenyl)-[1,1':2',1":4",1"' -Bitetraphenyl]-4-amine: 12.0g, 3-(2-naphthyl)phenylboronic acid: 5.3g, toluene: 84mL, ethanol: 21mL, potassium carbonate: 4.9g, water: 18mL, add four (triphenyl) (base phosphine) palladium: 0.4 g, refluxed and stirred for 14 hours. After cooling, methanol: 84 mL was added, the precipitated solid was collected by filtration, water: 70 mL, methanol: 70 mL were added to the solid, and the back flow was dispersed and washed for 1 hour. Collect the solid by filtration, add toluene: 140 mL, temporarily heat to 100°C, remove water and methanol, cool to 80°C, add silica gel: 7 g, activated clay: 7 g, stir for 1 hour, remove the solid by filtration, and concentrate the filtrate Acetone: 140 mL was added to the residue, stirred overnight at room temperature, and the solid was collected by filtration. The solid was recrystallized from a toluene/acetone mixed solvent to obtain N-(3'-(naphthalene-2-yl)-[ 1,1'-Biphenyl]-4-yl)-N-(4-(naphthyl)-2-yl)phenyl)-5'-phenyl-[1,1':2',1"- Yellow-white powder of bitetraphenyl]-4-amine: 11.3 g (yield: 79.6%).

[Chemical 14]

About the obtained yellow-white powder, the following 43 hydrogen signals were detected by ¹ H-NMR (CDCl ₃ ), and the structure was identified. δ(ppm)=8.09(1H), 8.01(1H), 7.77-7.92(8H), 7.43-7.73(19H), 7.21-7.38(10H), 7.04-7.13(4H).

硼烷-2-基)-[1,1’-聯苯基]-4-胺：29.5g、1,4-二

烷：200mL、磷酸鉀：32.1g、水：60mL，加入參(二亞苄基丙酮)二鈀：2.1g、三環己基膦：2.1g，回流攪拌14小時。放冷後，加入甲醇：200mL，藉由過濾採集析出之固體。對固體加入氯苯：360mL，暫時加熱至100℃，冷卻至80℃，加入矽膠：9g、活性白土：9g，攪拌1小時。藉由過濾去除固體，將濾液濃縮。對殘渣加入丙酮：360mL，於室溫攪拌一晚，藉由過濾採集固體，獲得N,4’-二苯基-[1,1’:2’,1”:4”,1”’-聯四苯基]-4”’-胺的黃白色粉體：30.6g(產率：85.5%)。 [Synthesis Example 7] <N,9,9-triphenyl-N-(4'-phenyl-[1,1':2',1":4",1"'-bitetraphenyl]-4 Synthesis of "'-yl)-9H-pyridin-2-amine (1-97)> In a reaction vessel, fill with 2'-chloro-[1,1';4',1"-triphenyl]: 20.0g, N-phenyl-4'-(4,4,5,5-tetramethyl-1,3,2-di

Boran-2-yl)-[1,1'-biphenyl]-4-amine: 29.5g, 1,4-di

Alkane: 200 mL, potassium phosphate: 32.1 g, water: 60 mL, ginseng (dibenzylideneacetone) dipalladium: 2.1 g, tricyclohexylphosphine: 2.1 g were added, and the mixture was stirred under reflux for 14 hours. After standing to cool, methanol: 200 mL was added, and the precipitated solid was collected by filtration. Chlorobenzene: 360 mL was added to the solid, temporarily heated to 100°C, cooled to 80°C, silica gel: 9 g, activated clay: 9 g, and stirred for 1 hour. The solids were removed by filtration and the filtrate was concentrated. Acetone: 360 mL was added to the residue, stirred overnight at room temperature, and the solid was collected by filtration to obtain N,4'-diphenyl-[1,1':2',1":4",1"'-biphenyl Yellow-white powder of tetraphenyl]-4"'-amine: 30.6 g (yield: 85.5%).

[Chemical 15]

In a reaction vessel, N,4'-diphenyl-[1,1':2',1":4",1"'-bitetraphenyl]-4"'-amine: 20.0 g, 2-Bromo-9,9-diphenyl-9H-pyrene: 18.5 g, toluene: 200 mL, sodium tertiary butoxide: 6.1 g, ginseng(dibenzylideneacetone)dipalladium: 0.1 g, tris(dibenzylideneacetone)dipalladium: 0.1 g, tris(dibenzylideneacetone)dipalladium 50% solution of tertiary butyl) phosphine in toluene: 0.2 g, refluxed and stirred for 14 hours. Cool to 80°C and remove solids by hot filtration using a diatomaceous earth-covered funnel. The filtrate was heated and stirred, and silica gel: 12 g and activated clay: 12 g were added at 80° C., and stirred for 1 hour. The solids were removed by filtration and the filtrate was concentrated. The residue was recrystallized from a toluene/acetone mixed solvent to obtain N,9,9-triphenyl-N-(4'-phenyl-[1,1':2',1":4",1" Yellow-white powder of '-bitetraphenyl]-4"'-yl)-9H-pyridin-2-amine (1-97): 21.4 g (yield: 64.1%).

[Chemical 16]

About the obtained yellow-white powder, the following 43 hydrogen signals were detected by ¹ H-NMR (CDCl ₃ ), and the structure was identified. δ(ppm)=7.64-7.71(5H), 7.58-7.60(1H), 7.51-7.53(1H), 7.41-7.48(6H), 7.30-7.38(3H), 7.14-7.24(21H), 6.98-7.09 (6H).

[Synthesis Example 8] <N-([1,1'-biphenyl]-4-yl)-5'-(naphthalene-2-yl)-N-(4-(naphthalen-2-yl)phenyl)-[1,1 Synthesis of ':2',1"-triphenyl]-4-amine (1-102)＞ A reaction vessel was charged with 4-bromo-2-chloro-1,1'-biphenyl: 31.0 g, 2-naphthaleneboronic acid: 22.0 g, toluene: 240 mL, ethanol: 60 mL, potassium carbonate: 24.1 g, and water: 80 mL, tetra(triphenylphosphine) palladium: 1.3 g was added, and the mixture was stirred under reflux for 15 hours. After standing to cool, liquid separation was performed, and the organic layer was washed with water. The organic layer was stirred, temporarily heated to 100° C. to confirm that there was no water, cooled to 80° C., silica gel: 20 g was added, and the mixture was stirred for 1 hour. The solids were removed by hot filtration and the filtrate was concentrated. The residue was recrystallized from a toluene/heptane mixed solvent to obtain a gray powder of 2-(2-chloro-[1,1'-biphenyl]-4-yl)naphthalene: 25.6 g (yield: 63.5%) ).

[Chemical 17]

硼烷-2-基)苯基)-[1,1’-聯苯基]-4-胺：24.8g、1,4-二

烷：160mL、磷酸鉀：27.0g、水：60mL，加入參(二亞苄基丙酮)二鈀：1.8g、三環己基膦：1.8g，回流攪拌12小時。放冷後進行濃縮。將殘留水之殘渣以甲苯萃取，對有機層依序以水、飽和食鹽水洗淨，以無水硫酸鎂乾燥。藉由過濾去除乾燥劑，將濾液進行攪拌、加熱，依80℃加入矽膠：20g。攪拌1小時，藉由熱過濾去除固體，將濾液濃縮。對殘渣藉由甲苯溶媒進行再結晶，獲得N-([1,1’-聯苯]-4-基)-5’-(萘-2-基)-[1,1’:2’,1”-聯三苯]-4-胺的黃白色粉體：26.0g(產率：78.0%)。In a reaction vessel, charged with 2(2-chloro-[1,1'-biphenyl]-4-yl)naphthalene: 20.0 g, N-(4-(4,4,5,5-tetramethyl- 1,3,2-two

Boran-2-yl)phenyl)-[1,1'-biphenyl]-4-amine: 24.8 g, 1,4-di

Alkane: 160 mL, potassium phosphate: 27.0 g, water: 60 mL, ginseng (dibenzylideneacetone) dipalladium: 1.8 g, tricyclohexylphosphine: 1.8 g were added, and the mixture was stirred under reflux for 12 hours. It was concentrated after standing to cool. The residual water residue was extracted with toluene, and the organic layer was washed with water and saturated brine in this order, and dried over anhydrous magnesium sulfate. The desiccant was removed by filtration, the filtrate was stirred and heated, and silica gel: 20 g was added at 80°C. Stir for 1 hour, remove solids by hot filtration, and concentrate the filtrate. The residue was recrystallized from a toluene solvent to obtain N-([1,1'-biphenyl]-4-yl)-5'-(naphthalen-2-yl)-[1,1':2',1 "-Triphenyl]-4-amine yellowish-white powder: 26.0 g (yield: 78.0%).

[Chemical 18]

In the reaction vessel, filled with N-([1,1'-biphenyl]-4-yl)-5'-(naphthalene-2-yl)-[1,1':2',1"-bitri Phenyl]-4-amine: 24.6 g, 2-(4-bromophenyl) naphthalene: 14.7 g, toluene: 250 mL, tert-butoxide sodium: 6.8 g, ginseng(dibenzylideneacetone)dipalladium was added : 0.4g, 50% toluene solution of tris(tert-butyl)phosphine: 0.4g, refluxed and stirred for 4 hours. After cooling to 80°C, use a funnel laid with diatomaceous earth to carry out hot filtration to remove solids. The filtrate was heated, Stir, add silica gel: 17 g, activated clay: 17 g at 80° C., stir for 1 hour. Remove the solid by filtration, and concentrate the filtrate. The residue is purified by crystallization and crystallization from a mixed solvent of toluene/acetone to obtain N-([1 ,1'-biphenyl]-4-yl)-5'-(naphthalen-2-yl)-N-(4-(naphthalen-2-yl)phenyl)-[1,1':2',1 "-Bitriphenyl]-4-amine (1-102) as a yellowish-white powder: 21.0 g (yield: 61.5%).

[Chemical 19]

About the obtained yellow-white powder, the following 39 hydrogen signals were detected by ¹ H-NMR (CDCl ₃ ), and the structure was identified. δ(ppm)=8.14(1H), 8.01(1H), 7.82-7.93(8H), 7.71-7.77(2H), 7.39-7.63(13H), 7.05-7.32(14H).

硼烷-2-基)苯基)-[1,1’-聯苯基]-4-胺：24.8g、甲苯：320mL、乙醇：90mL、碳酸鉀：21.9g、水：80mL，加入肆(三苯基膦)鈀：1.2g，回流攪拌13小時。放冷，藉由過濾採集析出之固體，加入甲醇：250mL、水：250mL，進行回流分散洗淨1小時後藉由過濾採集固體。於固體加入甲苯：750mL，進行攪拌，暫時加熱至100℃，確認去除甲醇、水後，冷卻至80℃。加入矽膠：10g，攪拌1小時，藉由熱過濾去除固體。將濾液濃縮，對殘渣藉由丙酮溶媒進行晶析，獲得N-([1,1’-聯苯]-4-基)-5’-苯基-[1,1’:2’,1”-聯三苯基]-4-胺的黃白色粉體：33.0g(產率：65.9%)。 [Synthesis Example 9] <N-([1,1'-biphenyl]-4-yl)-5'-phenyl-N-(4-(3-phenylnaphthalen-1-yl)phenyl)- Synthesis of [1,1':2',1"-triphenyl]-4-amine (1-103)> In a reaction vessel, filled with 2'-bromo-[1,1':4', 1"-bitriphenyl]: 32.7g, N-(4-(4,4,5,5-tetramethyl-1,3,2-di

Boran-2-yl)phenyl)-[1,1'-biphenyl]-4-amine: 24.8g, toluene: 320mL, ethanol: 90mL, potassium carbonate: 21.9g, water: 80mL, add 4 ( Triphenylphosphine) palladium: 1.2 g, and stirred under reflux for 13 hours. After standing to cool, the precipitated solid was collected by filtration, methanol: 250 mL, water: 250 mL were added, and the mixture was refluxed, dispersed and washed for 1 hour, and then the solid was collected by filtration. Toluene: 750 mL was added to the solid, and the mixture was stirred and heated to 100°C, and after confirming removal of methanol and water, the mixture was cooled to 80°C. Add silica gel: 10 g, stir for 1 hour, remove solids by hot filtration. The filtrate was concentrated, and the residue was crystallized from an acetone solvent to obtain N-([1,1'-biphenyl]-4-yl)-5'-phenyl-[1,1':2',1" -The yellowish-white powder of triphenyl]-4-amine: 33.0 g (yield: 65.9%).

[hua 20]

In a reaction vessel, filled with N-([1,1'-biphenyl]-4-yl)-5'-phenyl-[1,1':2',1"-bitriphenyl]-4 - Amine: 10.2 g, 1-(4-bromophenyl)-3-phenylnaphthalene: 7.0 g, toluene: 70 mL, tertiary sodium butoxide: 2.8 g, added palladium acetate: 0.1 g, tris (tertiary) 50% toluene solution of butyl) phosphine: 0.4g, refluxed and stirred for 4 hours. After cooling to room temperature, methanol was added, and the precipitated solid was collected by filtration. To the solid, toluene was added: 300 mL, and stirred and heated at 80° C. Silica gel: 7 g, activated clay: 7 g were added, and stirred for 1 hour. The solid was removed by hot filtration, and the filtrate was concentrated. The residue was recrystallized from a dichloromethane/acetone mixed solvent to obtain N-([1,1'- Biphenyl]-4-yl)-5'-phenyl-N-(4-(3-phenylnaphthalen-1-yl)phenyl)-[1,1':2',1"-terphenyl yl]-4-amine (1-103) as a white powder: 10.9 g (yield: 74.2%).

[Chemical 21]

About the obtained white powder, the following 41 hydrogen signals were detected by ¹ H-NMR (CDCl ₃ ), and the structure was identified. δ(ppm)=8.01-8.03(2H), 7.94-7.96(1H), 7.58-7.77(9H), 7.22-7.53(25H), 7.08-7.15(4H).

For the triaromatic amine compounds represented by the general formula (1) obtained in Synthesis Examples 1 to 9, the glass transition point was measured with a high-sensitivity differential scanning calorimeter (manufactured by Bruker AXS, DSC3100SA). The results are shown below. Compound of Synthesis Example 1: 107.1°C Compound of Synthesis Example 2: 131.2°C Compound of Synthesis Example 3: 129.7°C Compound of Synthesis Example 4: 110.0°C Compound of Synthesis Example 5: 127.9°C Compound of Synthesis Example 6: 109.5°C Compound of Synthesis Example 7: 136.2°C Compound of Synthesis Example 8: 109.1°C Compound of Synthesis Example 9: 118.7°C

The above measurement results show that the triaromatic amine compound represented by the general formula (1) used in the present invention has a glass transition point of 100° C. or higher, and the film state is stable.

Using the triaromatic amine compound represented by the general formula (1) obtained in Synthesis Examples 1 to 9, a vapor-deposited film with a film thickness of 100 nm was formed on an ITO substrate. 202) The HOMO level (ionization potential) is measured, and the results are shown below. Compound of Synthesis Example 1: 5.67eV Compound of Synthesis Example 2: 5.72eV Compound of Synthesis Example 3: 5.75eV Compound of Synthesis Example 4: 5.72eV Compound of Synthesis Example 5: 5.76eV Compound of Synthesis Example 6: 5.69eV Compound of Synthesis Example 7: 5.68eV Compound of Synthesis Example 8: 5.67eV Compound of Synthesis Example 9: 5.73 eV

It can be seen from the above measurement results that the triaromatic amine compounds represented by the general formula (1) obtained in Synthesis Examples 1 to 9 have a better energy level than the HOMO level of 5.4 eV possessed by general hole transport materials such as NPD and TPD. , and has good hole transport ability.

[Example 1] An organic EL device was produced using the compound (1-4) obtained in Synthesis Example 1. As shown in FIG. 10, the organic EL element is formed on the glass substrate 1 on which the reflective ITO electrode as the transparent anode 2 is formed in advance, and the hole injection layer 3, the first hole transport layer 4 and the second electrode are sequentially evaporated. The hole transport layer 5 , the light emitting layer 6 , the electron transport layer 7 , the electron injection layer 8 , the cathode 9 , and the capping layer 10 are fabricated.

Specifically, the glass substrate 1 on which ITO with a film thickness of 50 nm, a reflective film of silver alloy with a film thickness of 100 nm, and ITO with a film thickness of 5 nm were sequentially formed, was ultrasonically cleaned in isopropyl alcohol for 20 minutes, Drying was carried out on a hot plate heated to 250°C for 10 minutes. Then, after UV ozone treatment was performed for 15 minutes, this glass substrate with ITO was installed in a vacuum vapor deposition machine, and the pressure was reduced to 0.001 Pa or less. Next, the electron acceptor (Acceptor-1) of the following structural formula and the compound (1-4) obtained in Synthesis Example 1 were vapor-deposited into Acceptor-1:Compound (1-4)=3:97 according to the vapor deposition rate ratio Binary vapor deposition is performed at a high speed to form a hole injection layer 3 with a thickness of 10 nm covering the transparent anode 2 . On this hole injection layer 3, the compound (1-4) of Example 1 was formed as a first hole transport layer 4 with a film thickness of 140 nm. On this hole transport layer 4, the following compound (HTM-1) was formed as the second hole transport layer 5 with a film thickness of 5 nm. On the second hole transporting layer 5, the following compound (EMD-1) and the compound (EMH-1) of the following structural formula are formed into a compound (EMD-1) at a vapor deposition rate ratio: (EMH-1) Binary vapor deposition was performed at a vapor deposition rate of =5:95 to form a light-emitting layer 6 with a film thickness of 20 nm. On this light-emitting layer 6, the compound (ETM-1) of the following structural formula and the compound (ETM-2) of the following structural formula are converted into the compound (ETM-1) according to the evaporation rate ratio: (ETM-2)= Binary vapor deposition was performed at a vapor deposition rate of 50:50 to form an electron transport layer 7 with a film thickness of 30 nm. On this electron transport layer 7, lithium fluoride was formed as an electron injection layer 8 with a film thickness of 1 nm. On this electron injection layer 8, a magnesium-silver alloy was formed as a cathode 9 with a film thickness of 12 nm. Finally, the compound (CPL-1) of the following structure was formed into the capping layer 10 with a film thickness of 60 nm. About the produced organic EL element, the measurement of the light emission characteristic when a DC voltage was applied was performed in the atmosphere and normal temperature, and the result is shown in Table 1 together.

[Chemical 22]

[Chemical 23]

[Chemical 24]

[Chemical 25]

[Chemical 26]

[Example 2] In Example 1, an organic EL was produced under the same conditions except that the compound (1-58) of Synthesis Example 2 was used instead of the Compound (1-4) of Synthesis Example 1 as the material of the first hole transport layer 4 element. About the produced organic EL element, the measurement of the light emission characteristic when a DC voltage was applied was performed in the atmosphere and normal temperature, and the result is shown in Table 1 together.

[Example 3] In Example 1, an organic EL was produced under the same conditions except that the compound (1-59) of Synthesis Example 3 was used instead of the Compound (1-4) of Synthesis Example 1 as the material of the first hole transport layer 4 element. About the produced organic EL element, the measurement of the light emission characteristic when a DC voltage was applied was performed in the atmosphere and normal temperature, and the result is shown in Table 1 together.

[Example 4] In Example 1, an organic EL was produced under the same conditions except that the compound (1-69) of Synthesis Example 4 was used instead of the Compound (1-4) of Synthesis Example 1 as the material of the first hole transport layer 4. element. About the produced organic EL element, the measurement of the light emission characteristic when a DC voltage was applied was performed in the atmosphere and normal temperature, and the result is shown in Table 1 together.

[Example 5] In Example 2, an organic EL was produced under the same conditions except that the compound (1-83) of Synthesis Example 5 was used instead of the Compound (1-4) of Synthesis Example 1 as the material of the first hole transport layer 4 element. About the produced organic EL element, the measurement of the light emission characteristic when a DC voltage was applied was performed in the atmosphere and normal temperature, and the result is shown in Table 1 together.

[Example 6] In Example 1, an organic EL was produced under the same conditions except that the compound (1-96) of Synthesis Example 6 was used instead of the Compound (1-4) of Synthesis Example 1 as the material of the first hole transport layer 4 element. About the produced organic EL element, the measurement of the light emission characteristic when a DC voltage was applied was performed in the atmosphere and normal temperature, and the result is shown in Table 1 together.

[Example 7] In Example 1, an organic EL was produced under the same conditions except that the compound (1-97) of Synthesis Example 7 was used instead of the Compound (1-4) of Synthesis Example 1 as the material of the first hole transport layer 4. element. About the produced organic EL element, the measurement of the light emission characteristic when a DC voltage was applied was performed in the atmosphere and normal temperature, and the result is shown in Table 1 together.

[Example 8] In Example 1, an organic EL was produced under the same conditions except that the compound (1-102) of Synthesis Example 8 was used instead of the compound (1-4) of Synthesis Example 1 as the material of the first hole transport layer 4. element. About the produced organic EL element, the measurement of the light emission characteristic when a DC voltage was applied was performed in the atmosphere and normal temperature, and the result is shown in Table 1 together.

[Example 9] In Example 1, an organic EL was produced under the same conditions except that the compound (1-103) of Synthesis Example 9 was used instead of the compound (1-4) of Synthesis Example 1 as the material of the first hole transport layer 4 element. About the produced organic EL element, the measurement of the light emission characteristic when a DC voltage was applied was performed in the atmosphere and normal temperature, and the result is shown in Table 1 together.

[Comparative Example 1] For comparison, in Example 1, except that the compound (HTM-2) of the following structural formula was used instead of the compound (1-4) of the synthesis example 1 as the material of the first hole transport layer 4, the rest were the same conditions to fabricate an organic EL element. About the produced organic EL element, the measurement of the light emission characteristic when a DC voltage was applied was performed in the atmosphere and normal temperature, and the result is shown in Table 1 together.

[Chemical 27]

[Comparative Example 2] For comparison, in Example 1, except that the compound (HTM-3) of the following structural formula was used instead of the compound (1-4) of the synthesis example 1 as the material of the first hole transport layer 4, the rest were the same conditions to fabricate an organic EL element. About the produced organic EL element, the measurement of the light emission characteristic when a DC voltage was applied was performed in the atmosphere and normal temperature, and the result is shown in Table 1 together.

[Chemical 28]

The voltage, luminance, luminous efficiency and power efficiency in the Examples and Comparative Examples shown in Table 1 are the values when a current with a current density of 10 mA/cm ² flows. In addition, the life of the element is that when the light emission luminance at the start of light emission (initial luminance) is set to 2000 cd/m ² and constant current driving is performed, the light emission luminance decays to 1900 cd/m ² (equivalent to 95% when the initial luminance is set to 100%). : time until 95% decay).

[Table 1] first hole transport layer Voltage [V] Luminance [cd/m ² ] Luminous Efficiency [cd/A] Power efficiency [lm/W] Component life [h] Example 1 Compound (1-4) 3.50 1055 10.55 9.47 416 Example 2 Compound (1-58) 3.49 1033 10.33 9.30 398 Example 3 Compound (1-59) 3.49 1031 10.31 9.29 422 Example 4 Compound (1-69) 3.48 1070 10.71 9.68 407 Example 5 Compound (1-83) 3.46 1026 10.27 9.32 434 Example 6 Compound (1-96) 3.52 1046 10.46 9.34 418 Example 7 Compound (1-97) 3.50 1077 10.78 9.68 383 Example 8 Compound (1-102) 3.44 1016 10.16 9.27 488 Example 9 Compound (1-103) 3.43 999 9.99 9.17 536 Comparative Example 1 Compound (HTM-2) 3.58 897 8.97 7.88 328 Comparative Example 2 Compound (HTM-3) 3.54 876 8.77 7.79 353

As shown in Table 1, with regard to the voltage when a current with a current density of 10 mA/cm ² was passed, compared with 3.54 to 3.58 V of Comparative Examples 1 to 2, the Examples 1 to 9 exhibited a significantly low voltage of 3.43 to 3.52 V. . The luminous efficiency when a current with a current density of 10 mA/cm ² was flowed was significantly high efficiency of 9.99 to 10.78 cd/A in Examples 1 to 9 compared to 8.77 to 8.97 cd/A of Comparative Examples 1 to 2. In addition, in terms of electric power efficiency, compared with 7.79 to 7.88 lm/W of Comparative Examples 1 to 2, in Examples 1 to 9, a remarkably high efficiency of 9.17 to 9.68 lm/W was exhibited. Furthermore, in terms of device life (95% attenuation), it was found that Examples 1 to 9 exhibited significantly longer lifespans of 383 to 536 hours compared to 328 to 353 hours of Comparative Examples 1 to 2.

From the above results, it can be clarified that the triaromatic amine compound having the specific structure represented by the general formula (1) used as the hole transport layer, more preferably as the material of the first hole transport layer, is compared with The conventional triaromatic amine compound used in the comparative example has a large hole mobility, so as shown in Examples 1 to 9, the organic EL element of the present invention has a lower driving voltage than the organic EL element of the comparative example. , High luminous efficiency, and long-life organic EL elements. (Industrial Availability)

Compared with the conventional organic EL device, the organic EL device of the present invention using the triaromatic amine compound with a specific structure can improve the luminous efficiency and improve the durability of the organic EL device, so it can be extended to home appliances, for example. Chemicals or lighting purposes.

1: glass substrate 2: Transparent anode 3: hole injection layer 4: The first hole transport layer 5: The second hole transport layer 6: Light-emitting layer 7: Electron transport layer 8: Electron injection layer 9: Cathode 10: Overlay

FIG. 1 is a diagram showing the structural formulas of compounds 1-1 to 1-12 as an example of the triaromatic amine compound represented by the general formula (1). Fig. 2 is a diagram showing the structural formulas of compounds 1-13 to 1-24 as examples of the triaromatic amine compounds represented by the general formula (1). Fig. 3 is a diagram showing the structural formulas of compounds 1-25 to 1-36 as examples of the triaromatic amine compounds represented by the general formula (1). 4 is a diagram showing the structural formulas of compounds 1-37 to 1-48 as examples of the triaromatic amine compounds represented by the general formula (1). Fig. 5 is a diagram showing the structural formulas of compounds 1-49 to 1-60 as examples of the triaromatic amine compounds represented by the general formula (1). FIG. 6 is a diagram showing the structural formulas of compounds 1-61 to 1-72 as an example of the triaromatic amine compound represented by the general formula (1). 7 is a diagram showing the structural formulas of compounds 1-73 to 1-84 as examples of the triaromatic amine compounds represented by the general formula (1). 8 is a diagram showing the structural formulas of compounds 1-85 to 1-96 as examples of the triaromatic amine compounds represented by the general formula (1). FIG. 9 is a diagram showing the structural formulas of compounds 1-97 to 1-105 as an example of the triaromatic amine compound represented by the general formula (1). FIG. 10 is a diagram showing an example of the structure of the organic EL element of the present invention.

1: glass substrate

2: Transparent anode

3: hole injection layer

4: The first hole transport layer

5: The second hole transport layer

6: Light-emitting layer

7: Electron transport layer

8: Electron injection layer

9: Cathode

10: Overlay

Claims (5)

An organic electroluminescence element, which is between an anode and a cathode, and has at least a hole transport layer, a light-emitting layer, and an electron transport layer in order from the anode side, wherein the hole transport layer contains the following general formula ( 1) The triaromatic amine compound shown; [Chem. 1]

(In the formula, A represents a monovalent group represented by the following general formula (2-1); B represents a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group, or a substituted or unsubstituted condensation Aromatic group; C represents a monovalent group represented by the following general formula (2-1), a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group, or a substituted or unsubstituted condensed aromatic group base;) [hua2]

(In the formula, the dotted line part represents the bonding site; R ₁ represents a deuterium atom, a fluorine atom, a chlorine atom, a cyano group, a nitro group, a straight-chain or branched alkane with 1 to 6 carbon atoms that may have substituents group, cycloalkyl group with 5 to 10 carbon atoms that may have substituents, straight-chain or branched alkenyl groups with 2 to 6 carbon atoms that may have substituents, and 1 carbon atoms that may have substituents Linear or branched alkoxy groups of ~6, cycloalkoxy groups of 5 to 10 carbon atoms that may have substituents, substituted or unsubstituted aromatic hydrocarbon groups, substituted or unsubstituted aromatic heterocycles group, substituted or unsubstituted condensed polycyclic aromatic group, or substituted or unsubstituted aryloxy group; n is the number of R ₁ , representing an integer of 0 to 3; and, when n is 2 or 3, a plurality of The R ₁ bonded to the same benzene ring can be the same or different from each other, and can also be bonded to each other through a single bond, a substituted or unsubstituted methylene group, an oxygen atom, or a sulfur atom to form a ring; L ₁ represents substituted or unsubstituted Substituted aromatic hydrocarbons, substituted or unsubstituted aromatic heterocycles, or substituted or unsubstituted condensed polycyclic aromatic divalent groups; m is the number of L ₁ , representing an integer from 1 to 3; and, m When it is 2 or 3, L ₁ can be the same or different from each other; Ar ₁ and Ar ₂ can be the same or different from each other, representing a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group, or substituted or unsubstituted condensed polycyclic aromatic groups). The organic electroluminescence element according to claim 1, wherein the monovalent group represented by the above general formula (2-1) is a monovalent group represented by the following general formula (2-2);

(In the formula, Ar ₁ , Ar ₂ , L ₁ , m, n and R ₁ are defined in the same manner as in the general formula (2-1) above). The organic electroluminescence element according to claim 1, wherein the monovalent group represented by the above general formula (2-1) is a monovalent group represented by the following general formula (2-3);

(In the formula, Ar ₁ , Ar ₂ , n and R ₁ are defined in the same manner as in the above-mentioned general formula (2-1); p represents 0 or 1). The organic electroluminescence element according to claim 1, wherein the monovalent group represented by the above general formula (2-1) is a monovalent group represented by the following general formula (2-4);

(In the formula, Ar ₁ and Ar ₂ are defined in the same manner as in the above-mentioned general formula (2-1); p represents 0 or 1). The organic electroluminescence device according to any one of claims 1 to 4, wherein the hole transport layer is composed of two layers of a first hole transport layer and a second hole transport layer, and the first hole transport layer is composed of two layers. The transport layer system contains the triaromatic amine compound represented by the above-mentioned general formula (1).

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